Building something that lasts is rare. Building something that rewires an entire industry? That’s almost unheard of. But that’s exactly what Jim McKelvey did when he co-founded Square (now Block) with Twitter co-founder Jack Dorsey.

Today, Jim and Sammi talk about how Square went head-to-head with Amazon and won, why Jim believes most startups don’t understand what real innovation looks like, and the surprising psychology behind a piece of tech being just difficult enough to capture attention. Plus, they dive into his more recent ventures, Invisibly and Fastrials, and what serving as an independent director at the Federal Reserve taught him about the intersection of policy and entrepreneurship. Plus, his hot take on— and role in— tipping culture.

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Here’s what Sammi covers with Jim:

00:00 Jim McKelvey’s Social Currency

01:17 How Square Evolved From A Personal Painpoint

02:37 That Time Jim Stripped in a Business Pitch

05:13 The Psychology of Attention in Business

19:50 How Square Beat Amazon

31:21 Understanding Human Behavior and Social Pressure

32:17 Lessons From Jim’s Time as a Federal Reserve Director

38:19 Why Invisibly Failed, Profitably

40:28 Jim’s Newest Venture and Revolutionizing Drug Trials

45:48 Advice for Entrepreneurs in Regulated Industries

53:33 Tipping Culture and FinTech Predictions

58:24 How to Show Social Currency Some Love

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Jim McKelvey (Square) on How to Out-Compete a Goliath, Advice for “Wantrepreneurs,” and Economizing Drug Trials